Methyl 4-amino-3-iodobenzoate

Methyl 4-amino-3-iodobenzoate Property

Melting point:

86-91 °C (lit.)

Boiling point:

369.6±32.0 °C(Predicted)

Density 

1.826±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

0.41±0.10(Predicted)

form 

Crystalline Powder

color 

Beige

InChI

InChI=1S/C8H8INO2/c1-12-8(11)5-2-3-7(10)6(9)4-5/h2-4H,10H2,1H3

InChIKey

MRLVFVTVXSKAMX-UHFFFAOYSA-N

SMILES

C(OC)(=O)C1=CC=C(N)C(I)=C1

CAS DataBase Reference

19718-49-1(CAS DataBase Reference)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

29224985

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Methyl 4-amino-3-iodobenzoate Chemical Properties,Usage,Production

Definition

ChEBI: Methyl 4-amino-3-iodobenzoate is a benzoate ester.

Synthesis

General procedure for the synthesis of methyl 4-amino-3-iodobenzoate from methyl 4-aminobenzoate: dissolve methyl 4-aminobenzoate (5.0 g, 0.033 mol), benzyltrimethylammonium dichloroiodonate (22.1 g, 0.056 mol), and calcium carbonate (5.0 g, 0.050 mol) in a solvent mixture of dichloromethane (200 ml) and methanol (100 g). . The reaction mixture was heated to reflux overnight with stirring. Upon completion of the reaction, the solution was cooled to room temperature, washed with saturated sodium bisulfate solution, and the organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the crude product methyl 4-amino-3-iodobenzoate (9.6 g, quantitative yield), which was used in the subsequent reaction without further purification. The structure of the product was confirmed by 1H NMR (400 MHz, DMSO-d6): δ 3.75 (s, 3H), 6.09 (s, 2H), 6.75 (d, J = 8.59 Hz, 1H), 7.66 (dd, J = 8.59, 2.02 Hz, 1H), 8.11 (d, J = 2.02 Hz, 1H).

References

[1] Patent: WO2007/38331, 2007, A2. Location in patent: Page/Page column 30-31
[2] Patent: WO2007/103759, 2007, A2. Location in patent: Page/Page column 48
[3] European Journal of Medicinal Chemistry, 2019, p. 234 - 248
[4] European Journal of Organic Chemistry, 2001, # 24, p. 4607 - 4613
[5] Synlett, 2014, vol. 25, # 3, p. 399 - 402